David Letterman’s most outrageous late night moments

As reported earlier today, David Letterman announced his retirement on tonight’s episode of Late Show with David Letterman, joking that, “what this means now is that Paul and I can get married.” Watch the announcement below:

To celebrate his departure, here’s a look back at some of the most outrageous moments David Letterman face over the course of his 32-year-long late night career:

David Letterman’s first Late Night episode, February 1, 1982

Dave’s first late night show featured Bill Murray as a guest. Murray would go on to appear on Dave’s shows many more times over the years, including just last night when he arrived to hijack the Late Show.

Andy Kaufman, 1980

The surrealist comedian, Andy Kaufman, appeared on Letterman’s NBC show with professional wrestler Jerry “The King” Lawler, whom Kaufman had challenged to a match. Kaufman, who appeared in a neck brace, goaded Lawler until the professional wrestler slapped him across the face. When they returned from the commercial break, Kaufman let loose a tirade of profanities directed at Lawler (none of which are censored in this video, so it is decidedly NSFW).

Some 10 years after Kaufman’s death, it was revealed that Kaufman’s feud with Lawler was completely staged and the two were actually good friends.

The Bullhorn Incident, 1985

In 1985, protesting the fact that The Today Show received more advertising from NBC than his anniversary program had, David Letterman interrupted a primetime taping of the morning program yelling through a bullhorn that he wasn’t wearing any pants. The prank resulted in a long-lasting feud between Letterman and Bryant Gumbel.

Cher, 1986

In 1986, Cher appeared on the show for the first time, and started the evening by flipping Paul Shaffer the middle finger for playing “I Got You Babe” when she came out. Cher then began verbally sparring with Dave, and when he asked her why it took so long for her to agree to come on the show, she explained that she thought he was an a**hole. The moment is at around the 3:50 mark in the video.

Crispin Glover, 1987

In the most bizarre interview perhaps in all of late night history, Crispin Glover, promoting his film River’s Edge, came on Late Night wearing a wig, platform shoes and a wacky outfit. He proceeded to give a stuttering, irrational interview, culminating with him kicking at David Letterman’s head. Letterman cut the interview short and stomped off stage. Later, Glover claimed he was in character during the interview.

Madonna, 1994

On his CBS show, Late Show with David Letterman, Madonna appeared, tried to make Dave smell her underwear, dropped the F bomb some 14 times, and refused to leave the stage. Needless to say, the appearance made the news the next day.

Drew Barrymore, 1995

Not to be outdone by Madonna’s antics, Drew Barrymore was Dave’s guest on his birthday. Vowing to give him a birthday present he’d never forget, she leapt up onto his desk and flashed him. The moment is at about the 9:25 mark in the video.

Farrah Fawcett, 1997

In 1997, Farah Fawcett appeared on Late Show, and gave a rambling, incoherent interview. Later, she claimed on Howard Stern’s show that she was joking with Dave and responding to the audience.

Courtney Love, 2004

Courtney Love had her own Drew Barrymore moment. It was greeted with considerably less enthusiasm.

John McCain’s No Show, 2008

During the 2008 election, John McCain was scheduled to appear on Late Show, but canceled at the last minute, claiming he was en route to D.C. for government business. This was less than true, and in the middle of the episode, Letterman broadcast an internal CBS feed of McCain preparing for an interview with Katie Couric. McCain appeared on Dave’s show a month later.

Extortion attempt, 2009

In 2009, David Letterman revealed that he had been targeted in an extortion attempt, having received a letter threatening to expose his affairs with several co-workers if Letterman did not pay the extortionist $2 million. A CBS producer from 48 Hours and the ex-boyfriend of one of the women Letterman was involved with was later revealed to be the extortionist. He was caught through Letterman’s cooperation with the Manhattan District Attorney’s office, and Letterman addressed the situation on his show in a very frank admission:

Joaquin Phoenix, 2010

Promoting his film Two Lovers, a bearded Joaquin Phoenix appeared on Late Show and gave a completely incoherent and unresponsive interview. Letterman ended the interview by saying, “Joaquin, we’re sorry you couldn’t be here tonight. We owe an apology to Farrah Fawcett.” Phoenix later revealed that his behavior during the interview was part of a mockumentary, I’m Still Here, that he and Casey Affleck were filming at the time.